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Triethylamine → tert-butyl (3R)-4-(4-ethoxybutyl)-3-methylpiperazine-1-carboxylate

HRID 69117
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HRID 69117 반응식
C1(C)C=CC(S(O[CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH2:16][CH3:17])(=O)=O)=CC=1.[CH3:19][C@H:20]1[NH:25][CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(#N)C>[CH2:16]([O:15][CH2:14][CH2:13][CH2:12][CH2:11][N:25]1[CH2:24][CH2:23][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21][C@H:20]1[CH3:19])[CH3:17]
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2756811(R)-1-Boc-3-methylpiperazineHCID 866943224-Ethoxybutyl 4-methylbenzene-1-sulfonate

생성물 1

HCID 86694321tert-butyl (3R)-4-(4-ethoxybutyl)-3-methylpiperazine-1-carboxylate수율 93.7%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

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온도
90 °C

실험 절차

A mixture of 3 g of 4-ethoxybutyl p-toluenesulfonate, 2.65 g of tert-butyl (3R)-3-methylpiperazine-1-carboxylate, 3.07 mL of triethylamine, and 30 mL of acetonitrile was stirred at 90° C. for 3 hours. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 3.1 g of tert-butyl (3R)-4-(4-ethoxybutyl)-3-methylpiperazine-1-carboxylate.

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform/methanol)

출처 및 근거

ORD 기록
ord-7a16a80309be49a386bd3f3d8860fd8b
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822448B2

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